Sodium hydride → HCID 18406850, compound

HRID 1016404Notes

Reaction equation

HRID 1016404 reaction equation
[C:1]([C:5]1[C:6]([O:22]S(C2C=CC(C)=CC=2)(=O)=O)=[N:7][N:8]2[C:13]=1[CH:12]=[N:11][N:10]=[C:9]2[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])([CH3:4])([CH3:3])[CH3:2].[CH3:33][N:34]1[C:38]([CH2:39]O)=[N:37][CH:36]=[N:35]1.[H-].[Na+]>CN(C)C=O>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[C:9]1[N:8]2[N:7]=[C:6]([O:22][CH2:39][C:38]3[N:34]([CH3:33])[N:35]=[CH:36][N:37]=3)[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:13]2[CH:12]=[N:11][N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 18406935HCID 18406935, compound

Product 1

HCID 18406850HCID 18406850, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 21, step e) (0.4 g, 0.0009 mol) and (2-methyl-2H-[1,2,4]triazol-3-yl)methanol (0.12 g, 0.0011 mol) were dissolved in dry N,N-dimethylformamide (10 ml) under nitrogen and sodium hydride (60% wt in oil) (0.035 g, 0.0009 mol) was added. The solution was stirred at room temperature for 3 h after which solvent was removed in vacuo and the residue was purified using silica gel chromatography with 0%→60% ethyl acetate/dichloromethane as eluent. Trituration with isohexane and recrystallisation from ethyl acetate/isohexane gave the required product (0.137 g, mp=144° C.). Data for the title compound: 1H NMR (400 MHz, CDCl3) δ 1.50 (9H, s), 3.84 (3H, s), 5.48 (2H, s), 7.18-7.26 (1H, m), 7.27-7.35 (1H, m), 7.47 (1H, m), 7.87 (1H, s), 9.41 (1H, s); MS (ES+) m/e 400 [MH]+; Anal. Found: C, 57.30; H, 4.64; N, 24.64%. C19H19F2N7O requires: C, 57.14; H, 4.79; N, 24.55%.

Workup

  1. customwas removed in vacuo
  2. customthe residue was purified
  3. customTrituration with isohexane and recrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-e788dcec484c401a86043208586f4a24
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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